Organic Chemistry
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Evaluate whether the base LiCN (pKa of H—CN = 9.22) can favorably deprotonate a hydroxyl group (pKa of R—OH = 16.0).
Can the hydroxyl group of propan-2-ol be favorably deprotonated by the base potassium ethanolate?
Determine which alcohol in the given pair is more acidic. Explain your choice.
1-butanol and 2-chloro-1-butanol
2-propanol and 2-propanethiol
Determine which alcohol in the given pair is more acidic. Give an explanation for your choice.
2-fluoropropanol or 3-fluoropropanol
2-bromoethanol or 2-chloroethanol
Write IUPAC (systematic) names for the following alcohols:
Include stereochemistry if applicable.
Draw chemical structures corresponding to the following IUPAC names:
a. (S)-4-chloropent-4-en-2-olb. cis-cyclobutan-1,2-diol
For each pair of compounds, determine which of the two compounds has a higher water solubility. Give a brief explanation for your choice.(i) pentan-1-ol or cyclopentanol(ii) hexan-1-ol or phenol(iii) 3-ethylpentan-3-ol or heptan-2-ol(iv) pentan-2-ol or cyclopentane-1,3-diol(v)
For each pair of compounds, determine which compound boils at a higher temperature. Give a brief explanation for your predictions.(i) heptan-1-ol or 3,3-dimethylpentan-1-ol(ii) pentan-2-one or pentan-2-ol
Use IUPAC rules and write the molecule name for the given structure.
The given name is wrong, based on IUPAC rules. Provide the correct name of the compound below.
3,5-dimethyl-4-oxoheptan-2-ol
Draw the correct structure of (R, E)-5-methylhex-3-en-2-ol.
What is the structure of the molecule with an IUPAC name (1R,4S)-4-chlorocyclopent-2-en-1-ol?
What is the condensed structure of the given compounds?
i. 1-chloro-4-methylpent-1-yne
ii. 2,3-dimethylcyclopentan-1-ol
Determine the IUPAC name of the following alcohols and classify them as either primary (1°), secondary (2°), or tertiary alcohol (3°).
Predict which member is the least soluble in water: pentan-2-ol, butan-2-ol, or heptan-1-ol. Explain.
What are the IUPAC names of the diols given below?
(i) CH3CH2CH(OH)(CH2)3CH(OH)C(CH3)3
(ii) HO-(CH2)6-OH
(iii)
What are the systematic names of the following stereoisomers? (use cis/trans designation)
Can (CH3)3N favorably deprotonate an alcohol?
Note: The conjugate acid of (CH3)3N has a pKa of 9.80
Determine if the given base can deprotonate the hydroxyl group in an alcohol.
Suggest plausible mechanisms for proton exchanges between methanol molecules under the following conditions:
(i) acidic condition.
(ii) basic condition.